Cafedrine

{{short description|Chemical linkage of norephedrine and theophylline}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447926743

| IUPAC_name = (RS)-7-[2-[(1-hydroxy-1-phenylpropan-2-yl)amino]ethyl]-1,3-dimethylpurine-2,6-dione

| image = Cafedrine Structure.svg

| image_class = skin-invert-image

| width = 250px

| tradename = Akrinor, Bifort, Praxinor

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 58166-83-9

| ATC_prefix = C01

| ATC_suffix = CA21

| PubChem = 5489638

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104207

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4590188

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0UYY5V4U2Q

| synonyms = Caphedrine; Cafedrin; Caphedrin; Kafedrin; Norephedrino-ethyltheophylline; 7-(2-(β-Hydroxy-α-methylphen-ethylamino)ethyl)theophylline

| C=18 | H=23 | N=5 | O=3

| SMILES = C(CN[C@H]([C@H](O)C1=CC=CC=C1)C)N2C3=C(N(C)C(=O)N(C)C3=O)N=C2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H23N5O3/c1-12(15(24)13-7-5-4-6-8-13)19-9-10-23-11-20-16-14(23)17(25)22(3)18(26)21(16)2/h4-8,11-12,15,19,24H,9-10H2,1-3H3/t12-,15-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UJSKUDDDPKGBJY-WFASDCNBSA-N

}}

Cafedrine ({{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|BAN|British Approved Name}}), sold under the brand name Akrinor among others, is a chemical linkage of norephedrine and theophylline and is a cardiac stimulant and antihypotensive agent used to increase blood pressure in people with hypotension.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA205 | access-date=29 August 2024 | page=205}}{{cite book | title=Pharmaceutical Manufacturing Encyclopedia | publisher=Elsevier Science | series=Volumes 1-4 | year=2013 | isbn=978-0-8155-1856-3 | url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA785 | access-date=29 August 2024 | page=785}}{{cite book | vauthors = Morton IK, Hall JM | chapter = Calcitonin gene-related peptide receptor antagonist |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |date=1999 |publisher=Springer Netherlands |location=Dordrecht |isbn=9789401144391 |page=59 |chapter-url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA59 }}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | series=Index nominum | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA157 | access-date=29 August 2024 | page=157}} It has been marketed in Europe, South Africa, and Indonesia.{{cite web | title=Cafedrine | website=Drugs.com | url=https://web.archive.org/web/20180106120407/drugs.com/international/cafedrine.html | access-date=29 August 2024}}

There has been concern about cafedrine as a potential performance-enhancing drug and doping agent in sports.{{cite book | vauthors = Wilson W, Derse E | title=Doping in Elite Sport: The Politics of Drugs in the Olympic Movement | publisher=Human Kinetics | year=2001 | isbn=978-0-7360-0329-2 | url=https://books.google.com/books?id=wi2d4YyLh3wC&pg=PA15 | access-date=29 August 2024 | page=15}}